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15Five is an AI-powered performance management platform that combines generative AI, custom analytics, and human-centered design to help organizations drive engagement, performance, and retention. The platform includes 360° performance reviews, engagement surveys, goal tracking, manager coaching, and ongoing feedback tools.
In this role, you will serve as a Technical Solutions Consultant and strategic revenue partner for 15Five's sales team, covering both Mid-Market and Enterprise segments. You are not a demo-focused resource; instead, you are a solution builder and technical closer who works alongside Account Executives to secure deals by validating complex requirements, navigating HRIS integrations, and translating HR strategy into technical implementation.
Key Responsibilities:
**Strategic Co-Piloting & Deal Strategy:** Embed yourself in the sales cycle as a revenue partner, adapting to various sales styles and elevating deal strategy from quick-moving mid-market deals to long-cycle enterprise evaluations. Hold AEs accountable for deep discovery and push back on prep to ensure demonstrations are strategically aligned with prospect pain points. Manage expectations diplomatically when over-promises have been made, and execute the technical close by removing lingering technical friction and recognizing buying signals.
**Technical Execution & Integration Building:** Conduct high-stakes, audience-specific demonstrations tailored to agile mid-market teams or complex enterprise committees. Serve as the authority on the HRIS ecosystem (Workday, UKG, ADP, etc.), building and scoping API/SFTP integrations live to remove technical friction for IT stakeholders. Configure bespoke Proof of Concepts and environments that reflect prospect organizational culture. Confidently navigate security questionnaires (GDPR, SOC2, PII) and enterprise procurement processes.
**Content Creation & Market Intelligence:** Create micro-demos and annotated assets to enable internal champions. Act as a bridge between Sales and Product, influencing the roadmap by documenting product gaps, integration blockers, and market shifts.
You will report to the VP of Sales and Partnerships and work in a fast-paced, remote startup environment that emphasizes high standards, high accountability, and direct communication.
**Requirements:**
- Demonstrated desire or experience building products or API integrations; comfort with the technical "how it works" alongside sales execution
- Demonstrated ability to work with APIs, SFTP, SSO, and data migration; comfort using tools like Postman to validate workflows
- Sales grit and ambition; view yourself as part of a sales engine with understanding of deal velocity across market segments
- Ability to speak the language of HR buyers (calibration, competency matrices, flight risk) and translate for IT buyers
- Comfort in fast-paced environments where you may need to adapt during live demos or build custom environments to keep deals moving
- Familiarity with HRIS ecosystem tools (Workday, ADP, UKG) is expected; experience with Postman, Salesforce, Gong, and demo automation tools is valuable
